Studies on the Regioselective Nucleophilic Aromatic Substitution (SNAr) Reaction of 2-Substituted 3, 5-Dichloropyrazines

S Scales, S Johnson, Q Hu, QQ Do, P Richardson…

Index: Scales, Stephanie; Johnson, Sarah; Hu, Qiyue; Do, Quyen-Quyen; Richardson, Paul; Wang, Fen; Braganza, John; Ren, Shijian; Wan, Yadong; Zheng, Baojiang; Faizi, Darius; McAlpine, Indrawan Organic Letters, 2013 , vol. 15, # 9 p. 2156 - 2159

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Citation Number: 6

Abstract

Differences in regioselectivity were observed during the SNAr reaction of amines with unsymmetrical 3, 5-dichloropyrazines. This study revealed that when the 2-position of the pyrazine was occupied with an electron-withdrawing group (EWG), nucleophilic attack occurred preferentially at the 5-position. When the 2-position was substituted with an electron-donating group (EDG), nucleophilic attack occurred preferentially at the 3- ...